Acetonitrile → 4-[7-Phenyl-4-(prop-2-en-1-yl)-1,4-oxazepan-7-yl]phenol

HRID 596174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596174
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(#N)C.[CH2:25](Br)[CH:26]=[CH2:27]>C(N(CC)CC)C>[CH2:27]([N:12]1[CH2:11][CH2:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:15][CH2:14][CH2:13]1)[CH:26]=[CH2:25]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 7841Allyl bromideHCID 203266424-(7-Phenyl-1,4-oxazepan-7-yl)phenol--hydrogen chloride (1/1)

Produkt 1

HCID 203266444-[7-Phenyl-4-(prop-2-en-1-yl)-1,4-oxazepan-7-yl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

The mixture of 11.2 g of 7-(4-hydroxyphenyl)-7-phenylhexahydro-1,4-oxazepine hydrochloride, 110 ml of dry acetonitrile, 14.0 g of triethylamine and 5.05 g of allyl bromide is stirred at room temperature for 48 hours. It is evaporated and the residue partitioned between benzene and 2N aqueous sodium hydroxide. The aqueous layer is separated, combined with a further basic extraction of the benzene solution, and the combined aqueous solutions are adjusted to 9 pH of 4-6.3 with acetic acid. The solid which separates is collected, dried and converted to the hydrochloride in acetone (mp. 150°-153°). The free base is liberated again and crystalized from ethanol, to yield the 4-allyl-7-(4-hydroxyphenyl)-7-phenyl-hexahydro-1,4-oxazepine melting at 205°-207°.

Aufarbeitung

  1. customIt is evaporated
  2. customthe residue partitioned between benzene and 2N aqueous sodium hydroxide
  3. customThe aqueous layer is separated
  4. extractioncombined with a further basic extraction of the benzene solution
  5. customThe solid which separates is collected
  6. customdried
  7. customcrystalized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bf7174be5b8a46eda7c771bc098c6e34
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010166

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